Brad Feld

Category: Venture Capital

Author: Seth Levine, Mobius Venture Capital


Brad’s given me permission to co-opt his blog for the day.  I work for Brad (and had a great time recently up in Alaska “working”) which gives me an unusual vantage point from which to consider some of his posts on the world of VC.  After reading several of these posts (and of course living in this world with him) I came up with the great idea of suggesting to Brad that he write a post about deal splits and the notion of what investing “pro-rata” actually means.  Brad had an even better idea which was to have me write the post (which, of course, made my original idea seem not quite so brilliant). 


The question of what “pro-rata” means in the context of a deal seems, on its surface, pretty straight forward.  Simply put this question asks how much each investor intends to invest in a financing round.  However, as is often the case when you get two VCs in a room and ask them to decide on something, actually agreeing on what this is becomes another matter all together.  One investor’s view of the meaning of “playing their pro-rata” is often different from that of another.  Unfortunately, in many cases this isn’t discovered until late in a financing process leaving an entrepreneur scrambling to reset expectations and either make up a gap in a capital raise or placate an investor who believed they would get the chance to invest more in a round.  Ask most VCs and they’ll tell you everyone knows what pro-rata means (try this – its can be amusing); end up with confusion around this in the 11th hour of a financing and you’ll realize that this is definitely not the case.


The best way to illustrate the complexity of this concept is to take a look at a couple of examples.  Take the case of a Series A round for ProRata Corp.  Assume the post money on the deal is $8m and each investor, having invested $2m each, ends up owning 25% of the business.  Fast forward to the Series B financing and consider two scenarios.  In the first scenario there is no outside investor and the company raises $6m.  Logically, each investor would contribute $3m to the financing, as each was responsible for 50% of the prior financing round.  Note that this would leave them each owning just under 36% of the business post financing – meaning that by some definitions they actually played above their pro-rata amount because they have each increased their ownership in the business.  Now consider the same case where a new investor is brought into the mix in the Series B.  Assuming this investor takes $2m of the $6m round, is the pro-rata for the remaining investors $2m (half of the remaining $4m)?  It could also be $1.5m (which, in the $6m round would allow the investor to retain their 25% ownership).  Of course in that case there would be a shortfall.  I know this sounds crazy, but this exact situation happened to us about a month ago (and plenty of times prior to that).  Each of Mobius and the other existing investor was talking about contributing our pro-rata amount to the financing – our believing that this meant that the two existing investors would split the remainder of the round based on their relative ownership percentage; the other investor believing that they would retain their ownership percentage in the business. In that case Mobius made up the difference – we were strongly supportive of the business and happy to increase our ownership – however if we had not been in a position to do so, the company would have been left with a gap in their financing plan.


This example was actually pretty straightforward.  Things start to get much more complicated for a company that has raised multiple rounds of financing, has shareholders who own several classes of stock (common, junior preferred, senior preferred (perhaps with a change in their conversion ratio due to anti-dilution), warrants, etc.).  In those cases, what constitutes pro-rata? Even in our relatively simple example where all of the new money in a round is coming from existing investors this a complicated question.  Do the shareholders split the round based on their total as-converted common ownership?  Do they only count their senior preferred in the calculation? Do they include their entire preferred ownership position?  The different methods of calculating pro-rata in this case can lead to vastly different views on investment amounts.  This is important by itself, but becomes even more so in the case where a company is doing a down round financing where failure to participate pro-rata will lead to losing preference rights or some other penalty.  Interestingly within venture funds this is also an issue, as funds that have made cross fund investments (that is investments in the same company from more than one of their funds over time) also need to determine how to split an investment between funds.


There is no neat conclusion here.  The concept of pro-rata participation is something that sounds in theory like it should be pretty straightforward, but in practice rarely is.  Out of this confusion, the important point for entrepreneurs and investors alike is to make sure they have a discussion about participation amounts early in the investment process.  Discrepancies in expectations can always be dealt with more constructively if there is time to spare, rather than at the last minute.

When I wrote my first post on the structure and financial components of a typical venture capital investment – where I described Liquidation Preferences – I alluded to the concept of participating preferred as a maligned and typically hotly negotiated issue in many venture capital investments. In this post, I’m going to try to explain the notion of participating preferred (referred to hereafter as PP), how it works, and its financial and emotional impact on a deal. I’m not going to take sides, but rather try to give a broad perspective on it.

First – some history. I first encountered PP when several of the angel investments that I did in 1994 and 1995 matured to the point where they raised a round of institutional venture capital. Since I was living in Boston at the time, most of the VCs looking at my angel deals were east coast firms. In every single case, the initial term sheets each of these companies received included a PP feature – a “double dip” as my east coast lawyer called it. When we pushed back on the PP, we were told that all east coast term sheets had them (our lawyer told us it was negotiable, but that it was definitely an east coast standard request). The PP survived several of term sheet negotiations, but not all of them.

My east coast-centric world changed significantly after I moved to Colorado in 1996 and started doing venture capital. Because of geography and investment focus, I ended up working on more stuff on the west coast. There, I rarely saw a PP feature and was told flatly that PP was “an east coast term.” As the 1990’s marched on and the bubble started to build, I rarely saw a PP – even the east coast guys had dropped it from their standard term sheets.

After the bubble burst in 2001, PP was back – and this time on both coasts. Suddenly every term sheet I saw had a PP feature in it, regardless of the stage of the investment, type of business, or location of investor. It had once again become “a standard feature”, although it was now bi-coastal (or – more accurately – a red-blooded American term.)

So, with this as background, and before we dig into the actual mechanics of a PP, lets first recognize it for what it is – an economic feature in a venture investment. It’s not a standard term, nor is it something that is evil and should never be part of a deal. Unlike a liquidation preference which is rarely negotiable with a VC, a PP is almost always negotiable. There are even cases where it economically disadvantages an early stage investor who insists on it in the deal from the beginning. Importantly, there is not a consensus among investors on when a PP feature is appropriate in a deal and each firm approaches it from their own, unique perspective.

A PP is the right of an investor, as long as they hold preferred stock, to get their money back before anyone else (the “preference” part of PP), and then participate as though they owned common stock in the business (or, more technically, on an “as converted basis” – the “participation” part of PP). It takes a preferred investment, which acts as either debt or equity (where the investor has to make a choice of either getting their money back or converting their preferred shares to common), and turns it into something that acts both as debt and equity (where the investor both gets their money back and participates as if they had converted to common shares).

To illustrate, let’s take a simple case – a $5m Series A investment at $5m pre-money where the company is sold for $20m without any additional investments being made. In this case, the Series A investor owns 50% of the company. If they did not have a PP, they would get 50% of the return, or $10m. With the PP they get their $5m back and then get 50% of the remaining $15m ($7.5m), resulting in $12.5m to the Series A investor and $7.5m to everyone else. In this case, the Series A investor gets the equivalent of 62.5% of the return (rather than the 50% which is equivalent to their ownership stake). The PP results in a re-allocation of 12.5% of the exit value to the Series A investor.

Obviously, this can get much more complicated as you start to have multiple rounds of investments with a PP feature. A simple way to think about how the economics of a PP works is that the total dollar amount of the preference will come off the top of the exit value (and go to the investors); everyone will then convert into common stock and share the balance based on their ownership percentages. For example, assume a company raises $40m over 3 rounds where each round has a PP feature and the investors own 70% of the company. If this company is sold for $200m, the first $40m would go to the investors and the remaining $160m would be split 70% to investors / 30% to everyone else. In this case, the investors would get a total of $152m, ($40m + $112m, or 76% of the proceeds – 6% more then they would have gotten if there was no PP.)

If you sit and ponder the math, you’ll realize that a PP usually has material impact on the economics in low to medium return deals, but quickly becomes immaterial as the return increases (or – more specifically – as the ratio of the exit value to invested capital increases). For example, if a company is sold for $500m, a $10m PP re-allocates a small portion of the deal ($10m of the $500m) to the investors vs. the $40m of $200m or $5m of $20m in the other preceding examples. As a result, a PP usually only matters in a low to medium return situation. If a company is sold for less than paid in capital, the liquidation preference will apply and the participation feature will not come into play. If a company is sold for a huge amount of money, the PP won’t have much economic impact, as the preference feature of the PP becomes a small percentage of the deal total. In addition, in essentially every case, PP’s don’t apply in an IPO where preferred stock (of any flavor) is typically converted into common stock at the time of the offering.

As PP started showing up in more deals, some creative lawyer came out with a perversion on the preferred feature called a “cap on the participate” (also known as a “kick-out feature.”) In this case, the participation feature of the PP goes away once the investor holding the PP reaches a certain multiple return of capital. For example, assume a 3x cap on a PP in a $5m Series A investment. In this case, the investor would benefit from their PP until their proceeds from the deal reached $15m. Once they reached this level, their shares are no longer counted in the cap structure and the other shareholders share the remaining proceeds. Of course, the investor always has the option to convert their shares to common stock and give up their preferred return (but participate fully in the proceeds). Put another way, at a high enough valuation the investor is better off simply converting to common (in the current example at an exit value above $30m).

Participation caps, however, have a fundamental problem – they create a flat spot in most deal economics where the investor gets the same amount across a range of exit values. If we stay with the example above and assume a 50% ownership for the Series A, the PP would apply until the exit value reached $25m, at which point the investor receives $15m in proceeds. Between $25m and $30m, the investor would continue to receive this same $15m (this is the flat spot – it doesn’t matter whether the exit value is $26m or $29m, the investor would get $15m). At exit values above $30m, the investor would convert to common stock and take 50% of the proceeds (i.e., their as-converted share of the proceeds would exceed the $15m cap so they would be better off converting to common and taking this share of the exit value). This is an odd dynamic, since the common shareholders are clearly not indifferent to exit values in this flat spot, but the investor is (and consider a case where this flat spot was much larger than the one in the example above). Any way you cut it there is misalignment, at least for a range of outcomes, between the investor and the rest of the shareholders.

Another perversion is the “multiple participate”. In this case, the investor gets some multiple of his participate off the top of the transaction. For example, a 3x multiple participate on a $40m investment would mean the first $120m would go to the investor (and then the remaining proceeds would be distributed to the investor and the rest of the shareholders). This type of PP only appeared for a short while when investors were doing recapitalizations without actually going through the mechanics of recapitalizing the company (more about this in a future blog post).

Interestingly, there is a case to be made that PP in early financing rounds can actually end up disadvantaging early investors. The math on this gets complicated very quickly, but if you assume that every subsequent investment round has at least as favorable terms as the initial round (i.e., include a PP if the first round does) and that subsequent rounds include new investors there are many cases where the initial investor is actually disadvantaged by the existence of the PP (they would have been better off to have not put it in the initial round and because of that pushed for its exclusion from subsequent rounds). It’s counterintuitive, but it actually works out this way in a number of very common financing scenarios.

So – if PP simply relates to economics, why is it a term that brings out such emotion in entrepreneurs and investors alike? A close friend of mine who is an extremely successful entrepreneur recently told me “I’ve walked on every investment deal for any company that I’ve run that even smelled of multiple dips of participation – and spit back in the direction the term sheet came from!” We debated back and forth a while. For example, I asked him “would you take $5m for 33% of a company with no participate or 25% of a company with full participate?” He responded “I would go find a deal where I gave up 26.5% without a participate” which, while an emotional reaction, ironically reinforced my point that it was just economics. After pondering this term over the years, I’ve concluded that participating preferred is one of those terms that creates real tension between the entrepreneur and the investor – it forces the acknowledgement by the entrepreneur that a moderate return is not a success case for the investor and at the same time forces the investor to acknowledge that in those moderate cases they believe it is fair to receive a greater percentage of the proceeds at the expense of the entrepreneur.

VC Clichés

Aug 05, 2004

The two guys that work with me in Colorado – Chris Wand and Seth Levine – are visiting me in Alaska this week. We started joking about all the ridiculous things we (VCs) say on a regular basis. At the risk of exposing “super secret VC information”, I thought I’d write up a few of these phrases along with what they actually mean.

Oh – and on the topic of “giving away state secrets”, Matt Blumberg has a great post up on How to Negotiate a Term Sheet with a VC. This is a must read for anyone doing a venture financing. Matt – thanks a lot – look for my upcoming post on “How to give one of your star CEO’s a pay cut.”


  • We need to clarify our messaging: Our customers and prospects (and probably our employees) have no fucking idea what we do. This usually also means the VC doesn’t know what the company does.
  • We need to do a better job of filtering our sales prospects so we don’t waste our time on bad leads: Our marketing / demand generation sucks – we’re not targeting the right prospects. This is often a result of a nice pipeline, well presented and formatted, but with no resulting sales. Sometimes this is a marketing problem; sometimes this is a sales problem: often it’s both.
  • We need to strengthen our sales pipeline: We’re doing a crappy job in sales, but I’ve decided to be nice today either (a) because I’m in a good mood or (b) I don’t want to demoralize a team that knows it’s having trouble bringing it home. I put this phrase in the “yellow warning flag” category – you usually don’t get to hear it twice (unless your VC is a very blissful person).

Management Team

  • You need to focus on your core business fundamentals: You guys have no clue what your priorities are. This is a cliche born out of frustration that often leads up to a more serious discussion with the CEO about the systemic problems in the business (or more specifically, why the business is melting down.)
  • You need to get alignment among your management team: This one means two things: (1) One or more people on your team suck and need to go and (2) You – as CEO – are doing a sub-par job of leading the charge – and it shows.
  • You need to upgrade your management team: If you have the ability to read between the lines, this often means “if you don’t fix your management team, we’ll focus on ‘fixing’ you.”

Term Sheet Negotiations (Ode to Matt Blumberg’s Post)

  • We bring more than money to the table: Uh – yeah. What would that be again?
  • That’s an industry standard term: Hint – there are no industry standards in the venture business.
  • Don’t worry about pre-money – we’ll take care of you later: Did your mom ever says, “Honey – don’t worry about the water – c’mon in, it’s not too cold.”?
  • Don’t focus on percentages: This is kind of like saying to a 747 pilot “don’t bother paying attention to where the runway is – just land where ever you want.”
  • Don’t worry about that term, we’ll never actually enforce that: Um, right.

Reasons to Pass on Investments

  • It’s not in our sweet spot: I’m still looking for my own personal sweet spot – maybe that’s why I’m so sarcastic feeling today.

I received a number of comments, private emails, and a few links to my post on Venture Capital Deal Algebra. The consistent theme was “tell me more about how VC investments work.” As a result, I’m going to write a series of posts on the structural and financial components of a typical venture capital investment. I’m going to use a bottom up approach – talking about individual components over time and then tying them together in a comprehensive term sheet.

An important place to start is the concept of a liquidation preference. Fred Wilson hints at it in his post on valuation. A liquidation preference is a standand (and rarely negotiable part) of a VC investment. It’s the downside protection on an investment that VCs expect to have as a baseline of any equity investment.

The vast majority of VC investments are structured as preferred stock. It’s called preferred because it “sits in front of” the common stock (or is “preferred to the common”) where common stock is the plain vanilla stock that a company has. Typically in VC investments, founders receive common stock, employees receive either common stock or options to purchase common stock, and the VCs receive preferred stock. This preferred stock has a series of special rights which almost always include a liquidation preference. The liquidation preference means that the VC will have the option – in a liquidity event – of either receiving their liquidation preference as their return or converting into common stock and receiving their percentage ownership as their return.

Consider the following example. Acme Venture Capital (AVC) makes an investment in an established company called Homer Software that has been bootstrapped by the founders. Homer Software has shipped a product in an exciting market and generated $3m of revenue in the past 12 months. AVC invests $5m at a $10m pre-money valuation. As part of this investment, AVC and the founders of AVC agree to a 20% option pool for new employees that are going to be hired to be built into the pre-money valuation (see Venture Capital Deal Algebra if this doesn’t make sense). The result is that AVC owns 33.3% of the company, the founders own 46.7% of the company, and 20% is reserved for options for employees. In this example, AVC purchases Series A Preferred Stock that has a liquidation preference.

Now – consider two outcomes.

  1. Homer Software continues its rapid growth and is acquired for $100m. AVC has a choice – either receive the liquidation preference ($5m) or convert to common and receive 33.3% of the proceeds ($33.3m). Easy choice.
  2. Homer Software struggles and is acquired by a competitor for $9m. AVC again has a choice – either receive the liquidation preference ($5m) or convert to common and receive 33.3% of the proceeds ($3m). Again, easy choice.

When cash or public company stock is used in an acquisition, the valuation can be mathematically determined with certainty. However, when the acquirer is a private company, the valuation is much harder to determine and is often ambiguous as it depends on the value of the private company and the type of stock (common, preferred, junior preferred, or some other special class) being used. In these cases, the use of the liquidation preference is less clear cut and it’s critical that the company have objective, outside (independent) directors and experienced outside legal counsel to help with determining valuation.

One exception to the liquidity event is an IPO. Typically, an IPO will force the conversion of preferred stock to common stock, eliminating the liquidation preference. In most cases, the IPO event is an “upside liquidity event” so the need for the liquidation preference (and corresponding downside protection) is eliminated (although this is not always the case).

Next up – To Participate or Not (Participating Preferences) – an often maligned and typically hotly negotiated issue that is a more complex form of liquidation preference.

Fred Wilson wrote a useful post on valuation today. It reminded me of a document I had Dave Jilk write when he was doing some work for me. I decided to write this “bladon” (Blog Add-on) post – inspired by Fred. Please read Fred’s post first – it lays the groundwork for why VCs do things this way.

I’ve found that even sophisticated entrepreneurs didn’t necessary grasp how valuation math (or “deal algebra”) worked. VCs talk about pre-money, post-money, and share price as though these were universally defined terms that the average American voter would understand. To insure everyone is talking about the same thing, I started passing out this document. Recognize that this is about the math behind the calculations, not the philosophy of valuation (which Fred’s blog addresses).

In a venture capital investment, the terminology and mathematics can seem confusing at first, particularly given that the investors are able to calculate the relevant numbers in their heads. The concepts are actually not complicated, and with a few simple algebraic tips you will be able to do the math in your head as well, leading to more effective negotiation.

The essence of a venture capital transaction is that the investor puts cash in the company in return for newly-issued shares in the company. The state of affairs immediately prior to the transaction is referred to as “pre-money,” and immediately after the transaction “post-money.”

The value of the whole company before the transaction, called the “pre-money valuation” (and similar to a market capitalization) is just the share price times the number of shares outstanding before the transaction:

Pre-money Valuation = Share Price * Pre-money Shares

The total amount invested is just the share price times the number of shares purchased:

Investment = Share Price * Shares Issued

Unlike when you buy publicly traded shares, however, the shares purchased in a venture capital investment are new shares, leading to a change in the number of shares outstanding:

Post-money Shares = Pre-money Shares + Shares Issued

And because the only immediate effect of the transaction on the value of the company is to increase the amount of cash it has, the valuation after the transaction is just increased by the amount of that cash:

Post-money Valuation = Pre-money Valuation + Investment

The portion of the company owned by the investors after the deal will just be the number of shares they purchased divided by the total shares outstanding:

Fraction Owned = Shares Issued /Post-money Shares

Using some simple algebra (substitute from the earlier equations), we find out that there is another way to view this:

Fraction Owned = Investment / Post-money Valuation = Investment / (Pre-money Valuation + Investment)

So when an investor proposes an investment of $2 million at $3 million “pre” (short for premoney valuation), this means that the investors will own 40% of the company after the transaction:

$2m / ($3m + $2m) = 2/5 = 40%

And if you have 1.5 million shares outstanding prior to the investment, you can calculate the price per share:

Share Price = Pre-money Valuation / Pre-money Shares = $3m / 1.5m = $2.00

As well as the number of shares issued:

Shares Issued = Investment /Share Price = $2m / $2.00 = 1m

The key trick to remember is that share price is easier to calculate with pre-money numbers, and fraction of ownership is easier to calculate with post-money numbers; you switch back and forth by adding or subtracting the amount of the investment. It is also important to note that the share price is the same before and after the deal, which can also be shown with some simple algebraic manipulations.

A few other points to note:

  • Investors will almost always require that the company set aside additional shares for a stock option plan for employees. Investors will assume and require that these shares are set aside prior to the investment, thus diluting the founders.
  • If there are multiple investors, they must be treated as one in the calculations above.
  • To determine an individual ownership fraction, divide the individual investment by the post-money valuation for the entire deal.
  • For a subsequent financing, to keep the share price flat the pre-money valuation of the new investment must be the same as the post-money valuation of the prior investment.
  • For early-stage companies, venture investors are normally interested in owning a particular fraction of the company for an appropriate investment. The valuation is actually a derived number and does not really mean anything about what the business is “worth.”

I’ve looked at thousands (tens of thousands?) presentations pitching new businesses since the mid 1990’s. The vast majority of them suck. Unfortunately, it’s not Powerpoint’s fault (no – it wouldn’t be better if Freelance has become the standard).

It’s the content creators fault. Edward Tufte – a master of The Visual Display of Quantitative Information, thinks Powerpoint is evil and corrupts absolutely. Blogs like Beyond Bullets help reduce the corruption, but given that I’m trying to get a very specific set of information in a short period of time (usually 30 – 60 minutes), more specificity about what I think is “good” is probably helpful.

Several years ago, Chris Wand (one of the guys that works with me at Mobius Venture Capital) put together a list of questions that a pitch to a VC should address. The world would be a better place if all entreprenuers could automagically incorporate this outline into their pitches – at least to me.

Following are the questions to address.

– What is your big vision?
– What problem are you solving and for whom?
– Where do you want to be in the future?

– How big is the market opportunity you are pursuing and how fast is it growing?
– How established (or nascent) is the market?
– Do you have a credible claim on being one of the top two or three players in the market?

– What is your product/service?
– How does it solve your customer’s problem?
– What is unique about your product/service?

– Who are your existing customers?
– Who is your target customer?
– What defines an “ideal” customer prospect?
– Who actually writes you the check?
– Use specific customer examples where possible.

– What is your value proposition to the customer?
– What kind of ROI can your customer expect by using buying your product/service?
– What pain are you eliminating?
– Are you selling vitamins, aspirin or antibiotics? (I.e. a luxury, a nice-to-have, or a need-to-have)

– What does the sales process look like and how long is the sales cycle?
– How will you reach the target customer? What does it cost to “acquire” a customer?
– What is your sales, marketing and distribution strategy?
– What is the current sales pipeline?

– What is your cost to acquire a customer?
– How will this acquisition cost change over time and why?
– What is the lifetime value of a customer?

– Who is the management team?
– What is their experience?
– What pieces are missing and what is the plan for filling them?

– How do you make money?
– What is your revenue model?
– What is required to become profitable?

– What is your stage of development? Technology/product? Team? Financial metrics/revenue?
– What has been the progress to date (make reality and future clear)?
– What are your future milestones?

– What funds have already been raised?
– How much money are you raising and at what valuation?
– How will the money be spent?
– How long will it last and where will the company “be” on its milestones progress at that time?
– How much additional funding do you anticipate raising & when?

– Who is your existing & likely competition?
– Who is adjacent to you (in the market) that could enter your market (and compete) or could be a co-opted partner?
– What are their strengths/weaknesses?
– Why are you different?

– Who are your key distribution and technology partners (current & future)?
– How dependent are you on these partners?

– How does this fit w/ the investor’s portfolio and expertise?
– What synergies, competition exist with the investor’s existing portfolio?

– What assumptions are key to the success of the business?
– What “gotchas” could change the business overnight? New technologies, new market entrants, change in standards or regulations?
– What are your company’s weak links?

Fred Wilson and I are cross posting each other today (we must miss each other) – he had a good post this morning on how turn downs work in venture capital and then followed it with a followup post about what makes a great VC.

Fred’s post on telling the truth is right on the money. One of the most infuriating experiences an entrepreneur (or VC) has to get turned down from someone with a “blow off reason” (or no reason at all). Entrepreneurs get this all the time from VCs – but VCs also get it from each other (as potential co-investors when a VC looking at a new deal turns an existing VC’s deal down) or from LPs (when they decide not to invest in a VCs new fund). While it’s unreasonable to expect people to go into excruciating detail about why they are turning you down, I’ve have much more respect for people that will give me a clear, truthful, simple reason they aren’t interested vs. an elusive, twisted, convoluted – or passive and silent – rejection. I’d much rather hear that my baby is ugly (or that I’m ugly) then get blown off.

Fred’s post made me think of two pet peeves that I have – one around rejection and the other around honesty.

Concerning rejection – even worse than a “blow off turn down” is the “slow no”. VCs are the master of this – rather than turning you down, they string you along – never saying yes, but never saying no. My advice to entrepreneurs is to drive to a definitive yes or no and – if it’s a maybe – understand why and what you have to do to move it from either a maybe to a yes or a no. Now – a maybe is ok – as long as it’s supported with both action and elapsed time (e.g. talk to me again in three months). The ambigous or unclear maybe (which is really just a string along because the VC – or whoever is stringing you along) is simply unwilling to make a decision. That’s weak.

Concerning honesty – the title of Fred’s post made me think of the millions of times I’ve heard someone start a statement with “To tell you the truth, …” or “Honestly, …”. When ever I hear this, I want to jump up and down and scream in their face “No – don’t tell me the truth – I want you to fucking lie to me!” Until a month ago I bit my tongue, but I can no longer deal with it so I do jump up and down and scream something comparable. If you are going to tell me the truth, just do it. If you are going to lie to me, do it, tell me you lied, and then delete all my contact info from your universe since I don’t ever want to deal with you ever again.

I’ll end with another one that a friend joked with me about today – “You guys are 360 degrees apart.” Now – wtf does that mean?

Last week I had a meeting with a prospective limited partner (“Mr. X”) who is long time investor in venture capital funds. He’s extremely experienced, well respected, and has a phenomenal track record. He’s also very provocative, which always spices up a meeting like this.

As we were discussing the backgrounds of the various partners at Mobius Venture Capital, I made the statement that we all have had meaningful experience as entrepreneurs and technology executives (VP level or higher) prior to becoming venture capitalists.

X immediately asked me if I had any data to support my view that this was a good thing. He said “take the top 50 individual VCs (based on historical returns) and correlate their experience – what does it show?” I thought for a minute and ran through my head some of the great VCs I know. Before I reached a conclusion, X said “it’s random – totally random – there’s no correlation to performance.”

At first, this surprised me (I was about 50/50 in my quick mental sort when he answered for me). Then – as I thought more about it – I realized that operating experience is merely an attribute that someone has rather than an indicator of performance. Experience by itself (whether operating experience or venture capital experience) is not enough – I’ve certainly worked with some abysmal VCs who have a lot of “venture capital experience” (and I’ve also worked with some abysmal VCs who have plenty of operating experience).

I pushed on what he thought actually correlated with success. He responded that the great VCs he knew had a combination of incredible instincts honed by experience combined with the ability to quickly and accurately size up situations and draw effective conclusions. He labelled this “pattern matching” – which is a good phrase for this capability.

I think the combination is what is critical – neither operating experience or pattern matching alone is enough (e.g. “I’ve seen this before, but I don’t know what to do”).

I’m sitting in a technical advisory board meeting for one of my companies (Rally Software Development). I’m moblonging from my Danger – pretty cool (at least to me).

We’re having a great meeting. I’ve sat in on a bunch of these over the last 10 years since I started investing in (vs. running) software
companies. Often, these meetings are a complete waste of time because of some disconnect between the goal of the meeting, the group of people in the room, the facilitated process – or worse – the complete dominance of one or two people.

We’ve got 15 people in the room – 5 from Rally and 10 advisors. The
chemistry is awesome – Rally is about to go GA with the first version of their product so we’re dealing with tangibles (instead of the abstract of “what should we do, where should we go”). Management is facilitating well – leting people talk, but keeping them on topic. The richness of the discussion is noticeable to everyone involved – which causes the discussion / debate to feed on itself.

This is one of the funnest parts of this job – seeing / being involved with a group of people passionate about trying to create something new and revolutionary where six months ago there was nothing.